ATE167859T1 - ANTIPROLIFERATIVE 4H-NAPHTHO(1,2-B)PYRANE DERIVATIVES - Google Patents
ANTIPROLIFERATIVE 4H-NAPHTHO(1,2-B)PYRANE DERIVATIVESInfo
- Publication number
- ATE167859T1 ATE167859T1 AT92309169T AT92309169T ATE167859T1 AT E167859 T1 ATE167859 T1 AT E167859T1 AT 92309169 T AT92309169 T AT 92309169T AT 92309169 T AT92309169 T AT 92309169T AT E167859 T1 ATE167859 T1 AT E167859T1
- Authority
- AT
- Austria
- Prior art keywords
- alkyl
- phenyl
- optionally substituted
- hydroxy
- carboxy
- Prior art date
Links
- XGLHSMNFZCEVOV-UHFFFAOYSA-N 4h-benzo[h]chromene Chemical class C1=CC2=CC=CC=C2C2=C1CC=CO2 XGLHSMNFZCEVOV-UHFFFAOYSA-N 0.000 title 1
- 230000001028 anti-proliverative effect Effects 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- 125000004185 ester group Chemical group 0.000 abstract 2
- 125000001072 heteroaryl group Chemical group 0.000 abstract 2
- 125000001624 naphthyl group Chemical group 0.000 abstract 2
- 150000002825 nitriles Chemical class 0.000 abstract 2
- -1 trifluoromethoxy, carboxy Chemical group 0.000 abstract 2
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 abstract 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000002541 furyl group Chemical group 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000001544 thienyl group Chemical group 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/92—Naphthopyrans; Hydrogenated naphthopyrans
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Diabetes (AREA)
- Rheumatology (AREA)
- Transplantation (AREA)
- Epidemiology (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pain & Pain Management (AREA)
- Urology & Nephrology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Gastroenterology & Hepatology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Saccharide Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
A pharmaceutical compound of the formula <CHEM> in which n is 0, 1 or 2 and R<1> is attached at any of the positions 5, 6, 7, 8, 9 or 10, and each R<1> is halo, trifluoromethyl, C<5> PI <8> alkoxy, hydroxy, nitro, C<5> PI <8> alkyl, C<5> PI <8> alkylthio, hydroxy-C<5> PI <8> alkyl, hydroxy-C<5> PI <8> alkoxy, trifluoromethoxy, carboxy, -COOR5 where R5 is an ester group, -CONR6R7 or -NR6R7 where R6 and R7 are each hydrogen or C<5> PI <8>alkyl; R<2> is phenyl, naphthyl or heteroaryl selected from thienyl, pyridyl, benzothienyl, quinolinyl, benzofurangyl or benzimidazolyl, said phenyl, naphthyl and heteroaryl groups being optionally substituted, or R<2> is furanyl optionally substituted with C<5> PI <8> alkyl; R<3> is nitrile, carboxy, -COOR8 where R8 is an ester group, -CONR9R<1>0 where R9 and R<1>0 are each hydrogen or C<5> PI <8> alkyl, or R<1><1>SO<6>- where R<1><1> is C<5> PI <8> alkyl or optionally substituted phenyl; and R4 is -NR<1><2>R<1><3>, -NHCOR<1><2>, -N(COR<1><2>)<6> or -N=CHOCH<6>R<1><2> where R<1><2> and R<1><3> are each hydrogen or C<5> PI <8> alkyl optionally substituted with carboxy, <CHEM> where X is C<6> PI <8> alkylene, or -NHSO<6>R<1>4 where R<1>4 is C<5> PI <8> alkyl or optionally substituted phenyl; provided that when n is 0, R<3> is nitrile and R4 is -NH<6>, R<2> is not phenyl or phenyl substituted in the para-position with a single chloro, hydroxy or methoxy substituent; and salts thereof. este
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB919121358A GB9121358D0 (en) | 1991-10-09 | 1991-10-09 | Pharmaceutical compounds |
| GB929213058A GB9213058D0 (en) | 1992-06-19 | 1992-06-19 | Pharmaceutical compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ATE167859T1 true ATE167859T1 (en) | 1998-07-15 |
Family
ID=26299655
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT92309169T ATE167859T1 (en) | 1991-10-09 | 1992-10-08 | ANTIPROLIFERATIVE 4H-NAPHTHO(1,2-B)PYRANE DERIVATIVES |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US5284868A (en) |
| EP (1) | EP0537949B1 (en) |
| JP (1) | JPH05194477A (en) |
| KR (1) | KR100228841B1 (en) |
| CN (1) | CN1034938C (en) |
| AT (1) | ATE167859T1 (en) |
| AU (1) | AU658003B2 (en) |
| CA (1) | CA2079428A1 (en) |
| CZ (1) | CZ281688B6 (en) |
| DE (1) | DE69226060T2 (en) |
| DK (1) | DK0537949T3 (en) |
| ES (1) | ES2117035T3 (en) |
| FI (1) | FI924551A (en) |
| HU (1) | HU218916B (en) |
| IL (1) | IL103356A (en) |
| MX (1) | MX9205714A (en) |
| MY (1) | MY111368A (en) |
| NO (1) | NO301587B1 (en) |
| NZ (1) | NZ244627A (en) |
| PH (1) | PH30659A (en) |
| RU (1) | RU2071472C1 (en) |
| TW (1) | TW221292B (en) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9203497D0 (en) * | 1992-02-19 | 1992-04-08 | Lilly Industries Ltd | Pharmaceutical compounds |
| EP0599514A3 (en) * | 1992-11-18 | 1994-07-06 | Lilly Industries Ltd | Pyranoquinoline derivatives as inhibitors of cell proliferation. |
| GB9306062D0 (en) * | 1993-03-24 | 1993-05-12 | Lilly Industries Ltd | Pharmaceutical compounds |
| EP0619314A1 (en) * | 1993-04-09 | 1994-10-12 | Eli Lilly And Company | 4-Phenyl-4H- naphtho(2,1-b)pyran derivatives and their pharmaceutical use |
| WO1995008289A2 (en) * | 1993-09-16 | 1995-03-30 | Scimed Life Systems, Inc. | Percutaneous repair of cardiovascular anomalies and repair compositions |
| US5407955A (en) * | 1994-02-18 | 1995-04-18 | Eli Lilly And Company | Methods for lowering serum cholesterol and inhibiting smooth muscle cell proliferation, restenosis, endometriosis, and uterine fibroid disease |
| US5665591A (en) * | 1994-12-06 | 1997-09-09 | Trustees Of Boston University | Regulation of smooth muscle cell proliferation |
| CN1219872A (en) * | 1996-05-24 | 1999-06-16 | 血管技术药物公司 | Compositions and method for treating or preventing diseases of body passageways |
| IL119069A0 (en) | 1996-08-14 | 1996-11-14 | Mor Research Applic Ltd | Pharmaceutical composition comprising tyrphostins |
| ATE260269T1 (en) | 1999-11-05 | 2004-03-15 | Cytovia Inc | SUBSTITUTED 4H-CHROMENS AND SIMILAR COMPOUNDS AS KASPASIS ACTIVATORS AND APOPTOSIS INDUCTORS AND THE USE THEREOF |
| EP1392683B1 (en) * | 2001-05-16 | 2009-12-02 | Cytovia, Inc. | Substituted 4h-chromenes and analogs as activators of caspases and inducers of apoptosis and their use as anticancer agents |
| EP1392283A4 (en) | 2001-05-16 | 2004-10-20 | Cytovia Inc | Substituted coumarins and quinolines as caspase activators |
| US6858607B1 (en) | 2001-05-16 | 2005-02-22 | Cytovia, Inc. | 7,8-fused 4H-chromene and analogs as activators of caspases and inducers of apoptosis and the use thereof |
| EP1513515A2 (en) * | 2002-05-16 | 2005-03-16 | Cytovia, Inc. | Substituted 4h-chromenes, 2h-chromenes, chromans and analogs as activators of caspases and inducers of apoptosis and the use thereof |
| EP1509515A4 (en) * | 2002-05-16 | 2006-07-05 | Cytovia Inc | Substituted 4-aryl-4h-pyrrolo 2,3-h chromenes and analogs as activators of caspases and inducers of apoptosis and the use thereof |
| US20040127519A1 (en) * | 2002-12-12 | 2004-07-01 | Pharmacia Corporation | Method of using aminocyanopyridine compounds as mitogen activated protein kinase-activated protein kinase-2 inhibitors |
| US20040127511A1 (en) * | 2002-12-12 | 2004-07-01 | Pharmacia Corporation | Tricyclic aminocyanopyridine inhibitors of mitogen activated protein kinase-activated protein kinase-2 |
| NZ553688A (en) * | 2004-09-09 | 2011-05-27 | Florey Howard Inst | Enzyme inhibitors for the inhibition of insulin-regulated aminopeptidase |
| EP2532388A3 (en) * | 2005-02-16 | 2013-03-06 | Md Bioalpha Co., Ltd. | Pharmaceutical composition for the treatment or prevention of diseases involving obesity, diabetes, metabolic syndrome, neuro-degenerative diseases and mitochondria dysfunction diseases |
| US20080183282A1 (en) * | 2006-03-09 | 2008-07-31 | Saul Yedgar | Use of lipid conjugates for the coating of stents and catheters |
| US8263775B2 (en) | 2007-11-19 | 2012-09-11 | Howard Florey Institute | Insulin-regulated aminopeptidase (IRAP) inhibitors and uses thereof |
| EA015364B1 (en) * | 2009-03-18 | 2011-06-30 | Учреждение Российской Академии Наук Институт Элементоорганических Соединений Им. А.Н. Несмеянова Ран (Инэос Ран) | 6,6'-diisopropyl-8,8'-dimethyl-2,2'-dinitro-3,3'-bis(trifluoromethyl)-3h,3'h-[9,9']di[benzo(f)chromenyl]-5,10,5',10'-tetraole, inhibiting antitumor activity and a method for preparing thereof |
| WO2012062901A2 (en) * | 2010-11-12 | 2012-05-18 | Deutsches Krebsforschungszentrum (Dkfz) | Chromene derivatives and their analoga as wnt pathway antagonists |
| WO2013070998A1 (en) | 2011-11-10 | 2013-05-16 | Memorial Sloan-Kettering Cancer Center | TREATMENT OF OVARIAN CANCER WITH 2-AMINO-4H-NAPHTHO[1,2-b]PYRAN-3-CARBONITRILES |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU724509A1 (en) * | 1978-09-21 | 1980-03-30 | Пермский государственный фармацевтический институт | Method of preparing 2-aroyl-3h-naphtho/2,1-b/pyranones-3 |
| US5232942A (en) * | 1988-04-14 | 1993-08-03 | Yamanouchi Pharmaceutical Co., Ltd. | Q-2819 substance and the use thereof |
-
1992
- 1992-09-25 US US07/951,629 patent/US5284868A/en not_active Expired - Fee Related
- 1992-09-29 CA CA002079428A patent/CA2079428A1/en not_active Abandoned
- 1992-10-05 CZ CS923035A patent/CZ281688B6/en not_active IP Right Cessation
- 1992-10-05 IL IL103356A patent/IL103356A/en not_active IP Right Cessation
- 1992-10-05 AU AU26216/92A patent/AU658003B2/en not_active Ceased
- 1992-10-05 PH PH45043A patent/PH30659A/en unknown
- 1992-10-05 TW TW081107894A patent/TW221292B/zh active
- 1992-10-06 RU SU925052861A patent/RU2071472C1/en active
- 1992-10-06 NZ NZ244627A patent/NZ244627A/en unknown
- 1992-10-06 MX MX9205714A patent/MX9205714A/en not_active IP Right Cessation
- 1992-10-07 KR KR1019920018309A patent/KR100228841B1/en not_active IP Right Cessation
- 1992-10-07 MY MYPI92001807A patent/MY111368A/en unknown
- 1992-10-08 NO NO923910A patent/NO301587B1/en not_active IP Right Cessation
- 1992-10-08 HU HU9203183A patent/HU218916B/en not_active IP Right Cessation
- 1992-10-08 CN CN92111625A patent/CN1034938C/en not_active Expired - Fee Related
- 1992-10-08 FI FI924551A patent/FI924551A/en unknown
- 1992-10-08 EP EP92309169A patent/EP0537949B1/en not_active Expired - Lifetime
- 1992-10-08 JP JP4269002A patent/JPH05194477A/en active Pending
- 1992-10-08 DK DK92309169T patent/DK0537949T3/en active
- 1992-10-08 DE DE69226060T patent/DE69226060T2/en not_active Expired - Fee Related
- 1992-10-08 AT AT92309169T patent/ATE167859T1/en not_active IP Right Cessation
- 1992-10-08 ES ES92309169T patent/ES2117035T3/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP0537949A1 (en) | 1993-04-21 |
| NO923910D0 (en) | 1992-10-08 |
| KR100228841B1 (en) | 1999-11-01 |
| CZ281688B6 (en) | 1996-12-11 |
| ES2117035T3 (en) | 1998-08-01 |
| CA2079428A1 (en) | 1993-04-10 |
| PH30659A (en) | 1997-09-16 |
| NO923910L (en) | 1993-04-13 |
| TW221292B (en) | 1994-02-21 |
| MX9205714A (en) | 1993-04-01 |
| CZ303592A3 (en) | 1993-12-15 |
| MY111368A (en) | 1999-12-31 |
| IL103356A0 (en) | 1993-03-15 |
| EP0537949B1 (en) | 1998-07-01 |
| DK0537949T3 (en) | 1999-02-15 |
| IL103356A (en) | 1998-02-22 |
| HU218916B (en) | 2000-12-28 |
| AU2621692A (en) | 1993-04-22 |
| NZ244627A (en) | 1994-12-22 |
| FI924551A0 (en) | 1992-10-08 |
| HUT62281A (en) | 1993-04-28 |
| KR930007931A (en) | 1993-05-20 |
| JPH05194477A (en) | 1993-08-03 |
| DE69226060T2 (en) | 1998-11-19 |
| DE69226060D1 (en) | 1998-08-06 |
| NO301587B1 (en) | 1997-11-17 |
| CN1073437A (en) | 1993-06-23 |
| AU658003B2 (en) | 1995-03-30 |
| RU2071472C1 (en) | 1997-01-10 |
| CN1034938C (en) | 1997-05-21 |
| US5284868A (en) | 1994-02-08 |
| FI924551A (en) | 1993-04-10 |
| HU9203183D0 (en) | 1992-12-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| UEP | Publication of translation of european patent specification | ||
| REN | Ceased due to non-payment of the annual fee |